Phosphorus pentachloride → 5-Acetylamino-7,8-difluoro-1-tetralone

HRID 964689노트

반응식

HRID 964689 반응식
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:6]=1[CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O)(=[O:3])[CH3:2].P(Cl)(Cl)(Cl)(Cl)Cl>ClCCl>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[C:7]2[C:6]=1[CH2:13][CH2:14][CH2:15][C:16]2=[O:18])(=[O:3])[CH3:2]

참가 물질

4

반응물 2

HCID 24819Phosphorus pentachlorideHCID 105872254-(2-Acetylamino-4,5-difluorophenyl)butanoic acid

생성물 1

HCID 224495485-Acetylamino-7,8-difluoro-1-tetralone

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The compound obtained in (4) above (9.07 gm) was dissolved into 450 ml of dichloromethane. To the mixture was added 7.71 gm of phosphorous pentachloride while stirring at room temperature. After stirring for a further 1 hour, the reaction mixture was concentrated and dichloromethane was added to the residue. Dichloromethane was evaporated again and 500 ml of 1,2-dichloroethane and 9.88 gm of anhydrous aluminum chloride were added to the residue. The mixture was stirred for 1 hour at 70° C. and gently heated under reflux for 15 hours. The reaction product was poured into ice-cold water, extracted with chloroform, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was subjected to silica gel column chromatography using chloroform-methanol (50:1) as an eluant to obtain fractions containing the target compound. The fractions were concentrated to obtain 2.31 gm of the title compound.

후처리

  1. stirringAfter stirring for a further 1 hour
  2. concentrationthe reaction mixture was concentrated
  3. additiondichloromethane was added to the residue
  4. customDichloromethane was evaporated again
  5. addition500 ml of 1,2-dichloroethane and 9.88 gm of anhydrous aluminum chloride were added to the residue
  6. stirringThe mixture was stirred for 1 hour at 70° C.
  7. temperaturegently heated
  8. temperatureunder reflux for 15 hours
  9. additionThe reaction product was poured into ice-cold water
  10. extractionextracted with chloroform
  11. washwashed with saturated brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. customThe solvent was evaporated
  14. customto obtain fractions
  15. additioncontaining the target compound
  16. concentrationThe fractions were concentrated

출처 및 근거

ORD 기록
ord-a70dcfc7723b49b3adfdfb73d819e4a3
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05770605

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